GB744773A - Indole derivatives - Google Patents
Indole derivativesInfo
- Publication number
- GB744773A GB744773A GB8777/53A GB877753A GB744773A GB 744773 A GB744773 A GB 744773A GB 8777/53 A GB8777/53 A GB 8777/53A GB 877753 A GB877753 A GB 877753A GB 744773 A GB744773 A GB 744773A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indole
- ethyl
- benzyloxy
- benzyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- -1 morpholyl Chemical group 0.000 abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- 238000006722 reduction reaction Methods 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 239000012448 Lithium borohydride Substances 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 2
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- ZFQYTUAXLKKSRG-UHFFFAOYSA-N 2-(5-benzhydryloxy-1H-indol-3-yl)-N-benzylethanamine Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC=1)CCNCC1=CC=CC=C1 ZFQYTUAXLKKSRG-UHFFFAOYSA-N 0.000 abstract 1
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical group C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 abstract 1
- WKPDXBXNJWWWGQ-UHFFFAOYSA-N 5-benzyloxytryptamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1OCC1=CC=CC=C1 WKPDXBXNJWWWGQ-UHFFFAOYSA-N 0.000 abstract 1
- JCQLPDZCNSVBMS-UHFFFAOYSA-N 5-phenylmethoxy-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1OCC1=CC=CC=C1 JCQLPDZCNSVBMS-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- GUYPVIAWSXGZIQ-UHFFFAOYSA-N N,N-dibenzyl-2-(2-methyl-5-phenylmethoxy-1H-indol-3-yl)ethanamine Chemical compound CC=1NC2=CC=C(C=C2C=1CCN(CC1=CC=CC=C1)CC1=CC=CC=C1)OCC1=CC=CC=C1 GUYPVIAWSXGZIQ-UHFFFAOYSA-N 0.000 abstract 1
- CIEIVCHKEWJJKH-UHFFFAOYSA-N N,N-diethyl-3-(5-phenylmethoxy-1H-indol-3-yl)propan-1-amine Chemical compound C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC=1)CCCN(CC)CC CIEIVCHKEWJJKH-UHFFFAOYSA-N 0.000 abstract 1
- GDGPWPLNLPJTJN-UHFFFAOYSA-N N-butyl-N-[2-(5-phenylmethoxy-1H-indol-3-yl)ethyl]butan-1-amine Chemical compound C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC=1)CCN(CCCC)CCCC GDGPWPLNLPJTJN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- IDIJUWFVRXORPJ-UHFFFAOYSA-N n,n-dimethyl-2-(5-phenylmethoxy-1h-indol-3-yl)ethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1OCC1=CC=CC=C1 IDIJUWFVRXORPJ-UHFFFAOYSA-N 0.000 abstract 1
- YYZWLIHUCDJTCJ-UHFFFAOYSA-N n-benzyl-n-methyl-2-(5-phenylmethoxy-1h-indol-3-yl)ethanamine Chemical compound C=1C=CC=CC=1CN(C)CCC(C1=C2)=CNC1=CC=C2OCC1=CC=CC=C1 YYZWLIHUCDJTCJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises a (5-benzyloxy-3-indole)-alkylamine having the formula <FORM:0744773/IV(a)/1> wherein X is phenyl, halophenyl, lower alkoxyphenyl, or lower alkylphenyl, Y is hydrogen, phenyl, halophenyl, lower alkoxyphenyl or lower alkylphenyl, R1 and R2 are alike or different and represent hydrogen or alkyl, n is 0 or 1, and R3 and R4 are alike or different and represent hydrogen, alkyl, cycloalkyl, aralkyl or phenyl, at least one of R3 and R4 being other than hydrogen, or wherein R3 and R4 together with the - N = form a 5 or 6 atom monoheterocyclic amino radical, or an acid addition salt or quaternary ammonium salt thereof, the terms "lower alkyl" and "lower alkoxy" denoting radicals containing 1 to 8 carbon atoms. The invention also includes a process for the preparation of (benzyloxy-3-indole)-alkylamines which comprises reducing the carbonyl group of a (benzyloxy-3-indole)-alkanoylamide to a methylene group. Heterocyclic radicals which -NR3R4 can represent include piperidyl, morpholyl, pyrrolidyl and thiomorpholyl radicals. Suitable reducing agents are lithium aluminium hydride, lithium borohydride, sodium and alcohol, or hydrogen with a catalyst, preferably platinum. Suitable media for the catalytic reduction are tetrahydrofuran, ether, isopropyl ether, morpholine and dioxane, the reduction usually being effected at the boiling point of the solvent though temperatures from about 0 DEG to 100 DEG C. are suitable. The products may be isolated from the reaction mixture as the free base, the salt with an acid such as hydrochloric, hydrobromic, sulphuric, acetic, tartaric or citric, or as quaternary ammonium salts such as the methochloride, ethobromide and benzyl chloride. The starting materials may be prepared by the series of reactions set out in Specifications 720,584, 728,013, 744,765 and 744,772. The products are suitable starting materials for the production of (hydroxy-3-indole)-alkylamines, such as 5-hydroxytryptamine (serotonin) by the method of Specification 744,774. The description includes a preparation of a -3-(5-benzyloxyindole)-N-benzyl-N-methylacetamide by the method of example 1 of Specification 744,772. In example (1) 5-benzyloxy - 3 - [2 - (N - benzyl - N - methylamino)ethyl] - indole is prepared by reduction with lithium aluminium hydride of a -3-(5-benzyloxyindole) - N - benzyl - N - methylacetamide, and is converted to the hydrochloride or other salts. 5-Benzyloxy-3-(2-aminoethyl)-indole and its salts are prepared similarly. In an analogous manner are prepared (2) 5 - benzyloxy - 3 - [2 - (N.N - dibenzyl amino) - ethyl]indole; and (3) its hydrochloride; (4) 5 - benzyloxy - 3 - [2 - (N,N-dimethylamino) - ethyl] - indole; (5) 5 - benzyloxy - 3 - [2 - (1 - piperidino) - ethyl] - indole (a - 3 - (5 - benzyloxyindole) - acetopiperidide, for use as starting material, is obtained by the method of example (11) of Specification 744,772. A list is given of similar compounds containing 2 - piperidino - ethyl, 1 - methyl - 2 - piperidinoethyl, 2 - morpholinoethyl, 2 - pyrrolidinoethyl, 2 - (4 - thiomorpholino) - ethyl, 3 - piperidino - propyl, and 1 - ethyl - 3 - (1 - piperidino)-propyl groups, in some cases with 2-ethyl groups, which are prepared similarly; (6) 5-(p,p1 - dimethylbenzhydryloxy) - 3 - [1 - methyl-3 - (N,N - dibenzylamino) - propyl] - indole (the reduction being effected with lithium borohydride). A list of similar 5-alkylbenzyloxy-3-indole)-alkanoylamides, containing p-methylethyl and propyl substituents and N-substituents selected from isopropyl, benzyl and phenyl radicals; (7) 2-ethyl-5-(p,p1-dichlorobenzhydryloxy) - 3 - [2 - (N - methyl - N - benzylamino) - ethyl] - indole (the reduction being effected with sodium and alcohol). Similar (5-halobenzyloxy - 3 - indole) - alkylamines are mentioned containing p-bromo and p-iodo substituents and N-substituents selected from methyl, cyclohexyl, benzyl and isopropyl radicals; (8) 5 - (p,p1 - dimethoxybenzhydryloxy) - 3 - [3 - (N,N - dibenzylamino) - propyl]-indole, and similar (5 - alkoxybenzyloxy - 3-indole)-alkylamines containing p-methoxy and ethoxy groups and N-substituents selected from cyclohexyl, benzyl and ethyl radicals; (9) 5-benzyloxy - 3 - [3 - (N,N - diethylamino) - propyl] - indole and similar compounds containing N-substituents selected from methyl isopropyl and benzyl radicals; (10) 5-benzhydryloxy - 3 - [2 - (N - benzylamino) - ethyl] - indole and similar compounds containing substituted ethyl-indole groups and N-substituents selected from ethyl, cyclopentyl, methyl and phenyl radicals; (11) 5 - benzyloxy - 3 - [2 - (N,N - dibutylamino) - ethyl] - indole and similar compounds containing 2 - (N - benzylamino)-ethyl, 2 - (N,N - dicyclohexylamino) - ethyl, 2-(N - cyclohexylamino) - ethyl, 2 - (N - methylamino) - ethyl, 3 - (N - methyl - N - benzylamino) - propyl, and 1 - methyl - 3 - (N - benzylamino) - propyl radicals; (12) 5 - benzyloxy-3 - [2 - (N - benzyl - N - phenethylamino) - ethyl indole; and (12) 2 - methyl - 5 - benzyloxy - 3-[2 - (N,N - dibenzylamino) - ethyl] - indole.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US282273A US2804462A (en) | 1952-04-14 | 1952-04-14 | Alkylamines and preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB744773A true GB744773A (en) | 1956-02-15 |
Family
ID=23080766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8777/53A Expired GB744773A (en) | 1952-04-14 | 1953-03-30 | Indole derivatives |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2804462A (en) |
| DE (1) | DE1025877B (en) |
| GB (1) | GB744773A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168526A (en) * | 1960-04-20 | 1965-02-02 | Upjohn Co | Derivatives of 3-(2-nitroethyl)-indole |
| US3205236A (en) * | 1965-09-07 | Process of preparation of /j-alkylated tryptamines |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042684A (en) * | 1962-07-03 | J-ethtl-jj-nitrovinylindole | ||
| US3058992A (en) * | 1962-10-16 | Intermediates for the preparation of | ||
| US3014043A (en) * | 1957-02-08 | 1961-12-19 | Merck & Co Inc | Serotonin antagonists |
| US2995566A (en) * | 1957-02-08 | 1961-08-08 | Merck & Co Inc | Preparation of tryptamine derivatives |
| US3075986A (en) * | 1958-01-09 | 1963-01-29 | Rhone Poulenc Sa | (1-piperdidylalkyl) derivatives of 3-indole |
| GB944443A (en) * | 1959-09-25 | 1900-01-01 | ||
| US3155668A (en) * | 1960-04-11 | 1964-11-03 | Sterling Drug Inc | 1-[3-, 2-, and 1-indolyl)-lower-alkyl]-tertiary amines and intermediates therefor |
| US20100007190A1 (en) * | 2005-03-01 | 2010-01-14 | Eric Johnson | Chair back |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2703325A (en) * | 1951-12-06 | 1955-03-01 | Upjohn Co | Preparation of 5-benzyloxytryptamines |
| US2708197A (en) * | 1952-05-24 | 1955-05-10 | Upjohn Co | Preparation of (hydroxy-3-indole)-alkylamines |
-
1952
- 1952-04-14 US US282273A patent/US2804462A/en not_active Expired - Lifetime
-
1953
- 1953-03-30 GB GB8777/53A patent/GB744773A/en not_active Expired
- 1953-04-10 DE DEU2133A patent/DE1025877B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205236A (en) * | 1965-09-07 | Process of preparation of /j-alkylated tryptamines | ||
| US3168526A (en) * | 1960-04-20 | 1965-02-02 | Upjohn Co | Derivatives of 3-(2-nitroethyl)-indole |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1025877B (en) | 1958-03-13 |
| US2804462A (en) | 1957-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3135794A (en) | 1-(n, n-dibenzylamino)-2-[n'-(halo-loweralkanoyl)-n'-(substituted)]-loweralkylenediamines | |
| AU2003237599B2 (en) | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them | |
| CA2157397C (en) | Indole derivatives as 5-ht1-like agonists for use in migraine | |
| US3472870A (en) | Sulfonamidotryptamines | |
| US3466287A (en) | 1-((3-indolyl)-lower-alkyl)-4-substituted piperazines | |
| US2814625A (en) | 3-indolyl amino hydrocarbyl ketones | |
| GB744773A (en) | Indole derivatives | |
| US2708197A (en) | Preparation of (hydroxy-3-indole)-alkylamines | |
| US5726177A (en) | Indole-derived arylpiperazines as ligands for 5HT1 -like, 5HT1B and 5HT1D receptors | |
| US3720771A (en) | 3-substituted-1-phenyl-indolines and indolinones in composition for alleviating mentol depression | |
| CA1258069A (en) | 1-aminoalkyl-1h-indoles useful as analgesics, anti- rheumatics and anti-inflammatories | |
| SE454777B (en) | 5-SUBSTITUTED 3-AMINOALKYL-1H INDOLES, PROCEDURES FOR THE PREPARATION OF THESE AND A PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF MIGREN | |
| CA1115703A (en) | Piperidinopropyl derivatives | |
| US2870162A (en) | Production of certain tryptamines and compounds produced in the process | |
| US3043849A (en) | 3-(3-substituted amino-1-propenyl) indoles | |
| Macor et al. | Use of 2, 5-dimethylpyrrole as an amino-protecting group in an efficient synthesis of 5-amino-3-[(N-methyl-pyrrolidin-2 (R)-yl) methyl] indole | |
| FR2767527A1 (en) | Indolic phenyl piperazines having specific affinity for 5-HT1-like receptors | |
| GB1395243A (en) | Process for preparing piperidine derivatives | |
| US4980368A (en) | Tryptamine compounds, and methods of cerebrovascular treatment therewith | |
| US3953467A (en) | Pyrazole derivatives and process for preparing the same | |
| US2930797A (en) | 2-alkyl-3-indoleglyoxylamides | |
| US2821532A (en) | Reduction of carbonylic radicals in indolyl-3 compounds | |
| JPS597706B2 (en) | Calbostyril Yudou Tainoseizohou | |
| PL81987B1 (en) | ||
| US2852515A (en) | Tertiary-aminoalkyl substituted tetrazoles and preparation thereof |